JP2018509280A5 - - Google Patents
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- JP2018509280A5 JP2018509280A5 JP2017536812A JP2017536812A JP2018509280A5 JP 2018509280 A5 JP2018509280 A5 JP 2018509280A5 JP 2017536812 A JP2017536812 A JP 2017536812A JP 2017536812 A JP2017536812 A JP 2017536812A JP 2018509280 A5 JP2018509280 A5 JP 2018509280A5
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- Prior art keywords
- carbon dioxide
- adsorbent
- amine
- mixture
- support
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- CURLTUGMZLYLDI-UHFFFAOYSA-N carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 27
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 26
- 239000001569 carbon dioxide Substances 0.000 claims 26
- 239000003463 adsorbent Substances 0.000 claims 23
- 150000001412 amines Chemical group 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 14
- 150000002118 epoxides Chemical class 0.000 claims 13
- 239000002904 solvent Substances 0.000 claims 12
- 239000007787 solid Substances 0.000 claims 7
- 229920000768 polyamine Polymers 0.000 claims 6
- 239000007789 gas Substances 0.000 claims 5
- 238000010438 heat treatment Methods 0.000 claims 5
- 239000007795 chemical reaction product Substances 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 4
- 239000005977 Ethylene Substances 0.000 claims 3
- TZIHFWKZFHZASV-UHFFFAOYSA-N Methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 claims 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- 229920005862 polyol Polymers 0.000 claims 3
- 150000003077 polyols Chemical class 0.000 claims 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- 239000000725 suspension Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N Diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- -1 polyvinylamine Polymers 0.000 claims 2
- 239000000377 silicon dioxide Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 claims 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 claims 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 claims 1
- NPKKFQUHBHQTSH-UHFFFAOYSA-N 2-(decoxymethyl)oxirane Chemical compound CCCCCCCCCCOCC1CO1 NPKKFQUHBHQTSH-UHFFFAOYSA-N 0.000 claims 1
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical group CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 claims 1
- NVKSMKFBUGBIGE-UHFFFAOYSA-N 2-(tetradecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCCCOCC1CO1 NVKSMKFBUGBIGE-UHFFFAOYSA-N 0.000 claims 1
- SFJRUJUEMVAZLM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxymethyl]oxirane Chemical compound CC(C)(C)OCC1CO1 SFJRUJUEMVAZLM-UHFFFAOYSA-N 0.000 claims 1
- QECCQGLIYMMHCR-UHFFFAOYSA-N 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane Chemical compound C1OC1COCC(COCC1OC1)(CC)COCC1CO1 QECCQGLIYMMHCR-UHFFFAOYSA-N 0.000 claims 1
- KUAUJXBLDYVELT-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-(oxiran-2-ylmethoxy)propoxy]methyl]oxirane Chemical compound C1OC1COCC(C)(C)COCC1CO1 KUAUJXBLDYVELT-UHFFFAOYSA-N 0.000 claims 1
- VQMQXWYQIIUJIT-UHFFFAOYSA-N 2-[[4-(oxiran-2-ylmethoxymethyl)cyclohexyl]methoxymethyl]oxirane Chemical compound C1OC1COCC(CC1)CCC1COCC1CO1 VQMQXWYQIIUJIT-UHFFFAOYSA-N 0.000 claims 1
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-N,N-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 claims 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims 1
- JHLNERQLKQQLRZ-UHFFFAOYSA-N Calcium silicate Chemical compound [Ca+2].[Ca+2].[O-][Si]([O-])([O-])[O-] JHLNERQLKQQLRZ-UHFFFAOYSA-N 0.000 claims 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N Cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 claims 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N DETA Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims 1
- WPYCRFCQABTEKC-UHFFFAOYSA-N Diglycidyl resorcinol ether Chemical compound C1OC1COC(C=1)=CC=CC=1OCC1CO1 WPYCRFCQABTEKC-UHFFFAOYSA-N 0.000 claims 1
- LSHROXHEILXKHM-UHFFFAOYSA-N N'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims 1
- 241000282376 Panthera tigris Species 0.000 claims 1
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- 229920002873 Polyethylenimine Polymers 0.000 claims 1
- 239000004721 Polyphenylene oxide Substances 0.000 claims 1
- 229920001451 Polypropylene glycol Polymers 0.000 claims 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N TiO Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims 1
- 229960001124 Trientine Drugs 0.000 claims 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N Triethylenetetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 150000003973 alkyl amines Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 229910052918 calcium silicate Inorganic materials 0.000 claims 1
- 239000000378 calcium silicate Substances 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 229910021393 carbon nanotube Inorganic materials 0.000 claims 1
- 239000002041 carbon nanotube Substances 0.000 claims 1
- 229910002090 carbon oxide Inorganic materials 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 229910052570 clay Inorganic materials 0.000 claims 1
- 239000006185 dispersion Substances 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
- UPCIBFUJJLCOQG-UHFFFAOYSA-L ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium;dibromide Chemical compound [Br-].[Br-].CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC UPCIBFUJJLCOQG-UHFFFAOYSA-L 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 239000000446 fuel Substances 0.000 claims 1
- CTKINSOISVBQLD-UHFFFAOYSA-N glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims 1
- 230000000887 hydrating Effects 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 229920000083 poly(allylamine) Polymers 0.000 claims 1
- 229920000647 polyepoxide Polymers 0.000 claims 1
- 229920000570 polyether Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000011164 primary particle Substances 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propanol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- 238000010926 purge Methods 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims 1
- 229910001929 titanium oxide Inorganic materials 0.000 claims 1
- 238000004642 transportation engineering Methods 0.000 claims 1
- 239000010457 zeolite Substances 0.000 claims 1
Claims (15)
(b)エチレン又はプロピレンを形成するための十分な条件下で、酸塩基触媒又はゼオライト触媒の存在下で前記ジメチルエーテルを加熱すること;
化学品の原料として又は輸送燃料として使用するための、高級オレフィン、合成炭化水素、芳香族、又はそれらから生成される生成物を得るための十分な条件下で、前記エチレン及び/又は前記プロピレンを転化すること;並びに
エタノール又はプロパノールを形成するための十分な条件下で前記エチレン又はプロピレンを水和すること
をさらに含む、請求項14に記載の方法。
(A) dehydrating said methanol under conditions sufficient to produce dimethyl ether ; or
(B) heating the dimethyl ether in the presence of an acid-base catalyst or a zeolite catalyst under conditions sufficient to form ethylene or propylene;
Under conditions sufficient to obtain higher olefins, synthetic hydrocarbons, aromatics, or products produced therefrom, for use as a raw material for chemicals or as a transportation fuel, the ethylene and / or the propylene are used. 15. The method of claim 14 , further comprising: converting; and hydrating the ethylene or propylene under conditions sufficient to form ethanol or propanol.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562102511P | 2015-01-12 | 2015-01-12 | |
US62/102,511 | 2015-01-12 | ||
PCT/US2016/012663 WO2016114991A1 (en) | 2015-01-12 | 2016-01-08 | Regenerative adsorbents of modified amines on solid supports |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2018509280A JP2018509280A (en) | 2018-04-05 |
JP2018509280A5 true JP2018509280A5 (en) | 2018-12-13 |
JP6663918B2 JP6663918B2 (en) | 2020-03-13 |
Family
ID=55405448
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017536812A Active JP6663918B2 (en) | 2015-01-12 | 2016-01-08 | Renewable adsorbents of modified amines on solid supports |
Country Status (7)
Country | Link |
---|---|
US (3) | US10751689B2 (en) |
EP (1) | EP3244993B1 (en) |
JP (1) | JP6663918B2 (en) |
KR (1) | KR20170127416A (en) |
AU (1) | AU2016207044B2 (en) |
CA (1) | CA2973572C (en) |
WO (1) | WO2016114991A1 (en) |
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WO2004054708A2 (en) | 2002-12-18 | 2004-07-01 | University Of Ottawa | Amine modified adsorbent, its preparation and use for dry scrubbing of acid gases |
US6908497B1 (en) | 2003-04-23 | 2005-06-21 | The United States Of America As Represented By The Department Of Energy | Solid sorbents for removal of carbon dioxide from gas streams at low temperatures |
US7608743B2 (en) | 2005-04-15 | 2009-10-27 | University Of Southern California | Efficient and selective chemical recycling of carbon dioxide to methanol, dimethyl ether and derived products |
KR101495085B1 (en) | 2005-04-15 | 2015-02-24 | 유니버시티 오브 써던 캘리포니아 | Efficient and selective conversion of carbon dioxide to methanol, dimethyl ether and derived products |
US7795175B2 (en) | 2006-08-10 | 2010-09-14 | University Of Southern California | Nano-structure supported solid regenerative polyamine and polyamine polyol absorbents for the separation of carbon dioxide from gas mixtures including the air |
US7906559B2 (en) | 2007-06-21 | 2011-03-15 | University Of Southern California | Conversion of carbon dioxide to methanol and/or dimethyl ether using bi-reforming of methane or natural gas |
EP2266680A1 (en) | 2009-06-05 | 2010-12-29 | ETH Zürich, ETH Transfer | Amine containing fibrous structure for adsorption of CO2 from atmospheric air |
JP5646892B2 (en) * | 2010-07-01 | 2014-12-24 | 旭化成株式会社 | Carbon dioxide absorbent and method for separating carbon dioxide using the same |
US8557027B2 (en) | 2010-12-22 | 2013-10-15 | Exxonmobil Research And Engineering Company | Epoxy-amine acid gas adsorption-desorption polymers and oligomers, processes for preparing same, and uses thereof |
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2016
- 2016-01-08 CA CA2973572A patent/CA2973572C/en active Active
- 2016-01-08 US US14/991,886 patent/US10751689B2/en active Active
- 2016-01-08 JP JP2017536812A patent/JP6663918B2/en active Active
- 2016-01-08 EP EP16705859.3A patent/EP3244993B1/en active Active
- 2016-01-08 WO PCT/US2016/012663 patent/WO2016114991A1/en active Application Filing
- 2016-01-08 KR KR1020177022258A patent/KR20170127416A/en not_active Application Discontinuation
- 2016-01-08 AU AU2016207044A patent/AU2016207044B2/en active Active
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2019
- 2019-02-08 US US16/271,245 patent/US10953384B2/en active Active
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2021
- 2021-03-11 US US17/199,252 patent/US20210197172A1/en not_active Abandoned
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